Use of isosorbide monoesters as thickeners

ABSTRACT

The use of one or more compounds of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which 
             R is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms
 
as thickeners is described.
 
           
         
       
    
     The use is preferably in cosmetic, dermatological or pharmaceutical compositions, in crop protection formulations, in washing or cleaning compositions or in paints or coatings.

The present invention relates to the use of isosorbide monoesters as thickeners.

In industry, thickeners are used to adjust the viscosity of products such as, for example, cosmetic, dermatological or pharmaceutical compositions, crop protection formulations, washing or cleaning compositions or paints or coatings in a targeted manner. Numerous thickeners which can be used for this purpose are known. These thickeners may have been produced synthetically, or they may be based on natural raw materials.

However, a disadvantage of the use of many synthetically produced thickeners, for example synthetic polymers, is that, frequently, their preparation is expensive and based on synthetic raw materials. In contrast, a disadvantage of the use of many thickeners based on natural raw materials is that the appearance of many products comprising such thickeners is in need of improvement.

Accordingly, it was an object of the invention to provide thickeners which do not have the disadvantages mentioned above or which improve these at least in part and which additionally have an advantageous thickener performance.

Surprisingly, it has now been found that this object is achieved by compounds of the formula (I)

in which R is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms.

Accordingly, the invention provides the use of one or more compounds of the formula (I)

in which R is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms as thickeners.

The compounds of the formula (I) are based on renewable raw materials such as, for example, on isosorbide, which can be obtained from sugar. They can be prepared in a simple manner by methods familiar to the person skilled in the art, for example by esterification of isosorbide with an acid component such as a carboxylic acid. The appearance of the products comprising the compounds of the formula (I) is not negatively affected by their presence. For example, compared to the use of xanthan gum which, as natural thickener, frequently yields products having a “brittle” or irregular or rough surface, using the compounds of the formula (I) it is possible to prepare thickened products having a smooth surface.

Compositions which are based at least in part on renewable raw materials and can be used as thickeners are already known.

WO 2010/108738 A2 (Evonik) describes formulations which are used to clean and care for human or animal body parts and comprise sorbitancarboxylic esters, where the carboxylic acid portion of the sorbitancarboxylic ester is derived from a carboxylic acid containing 6 to 10 carbon atoms and the sorbitancarboxylic esters have a hydroxyl value of more than 350, and the use of the sorbitancarboxylic esters mentioned as viscosity regulators, care active ingredient, foam booster or solubilizer in cleaning or care formulations.

Compounds of the formula (I) can be prepared, for example, by methods familiar to the person skilled in the art. For example, the compounds of the formula (I) can be prepared by esterification of isosorbide by customary methods known to the person skilled in the art, with both isosorbide for its part and also the acid components used for esterification once more being commercially available.

Preferably, the radical R in the one or more compounds of the formula (I) is a straight-chain saturated alkyl radical having 7 to 9 carbon atoms.

Particularly preferably, the radical R in the one or more compounds of the formula (I) is a straight-chain saturated alkyl radical having 7 carbon atoms.

According to the invention, the one or more compounds of the formula (I) can be used on their own or in compositions comprising one or more other substances as thickeners. Hereinbelow, these compositions are referred to as “compositions A”.

In a preferred embodiment of the invention, the compositions A comprise one or more compounds of the formula (I) and additionally one or more other substances selected from the group consisting of sorbitol, sorbitol esters (sorbitol esters can be mono-, di-, tri-, tetra-, penta- and/or hexaesters), sorbitan, sorbitan esters (sorbitan esters can be mono-, di-, tri- and/or tetraesters), isosorbide, isosorbide diesters and carboxylic acids. “Sorbitan” can be, for example, 1,4- or 1,5-sorbitan. Both the carboxylic acids themselves and the carboxylic acids on which the acid components of the esters mentioned are based correspond to the formula RCOOH in which R has the meaning given for formula (I) and is preferably a straight-chain saturated alkyl radical having 7 carbon atoms, i.e. the carboxylic acid RCOOH is preferably caprylic acid.

In a particularly preferred embodiment of the invention, the compositions A comprise one or more compounds of the formula (I) and additionally

-   I) isosorbide and -   II) one or more isosorbide diesters of the formula (II)

-   -   where R has the meaning given above for formula (I) and where         the isosorbide diester is preferably isosorbide dicaprylate.

From among these compositions, the compositions A just mentioned preferably comprise one or more compounds of the formula (I) and additionally

-   I) from 0.05 to 0.7, preferably from 0.1 to 0.7 and particularly     preferably from 0.2 to 0.5 part by weight of isosorbide and -   II) from 0.1 to 1.0, preferably from 0.2 to 1.0 and particularly     preferably from 0.4 to 0.8 part by weight of the one or more     isosorbide diesters of the formula (II), where the isosorbide     diester is preferably isosorbide dicaprylate,     in each case based on 1.0 part by weight of the one or more     compounds of the formula (I) and preferably based on 1.0 part by     weight of isosorbide monocaprylate.

In a preferred embodiment of this embodiment of the invention, the compositions A just mentioned comprise either no carboxylic acid RCOOH or up to 0.1, preferably 0.001 to 0.05 and particularly preferably 0.002 to 0.01 part by weight of carboxylic acid RCOOH, where R has the meaning given for formula (I) and where the carboxylic acid is preferably caprylic acid, based on 1.0 part by weight of the one or more compounds of the formula (I) and preferably based on 1.0 part by weight of isosorbide monocaprylate.

In a further particularly preferred embodiment of the invention, the compositions A comprise one or more compounds of the formula (I) and one or more sorbitan esters of sorbitan and carboxylic acids R^(a)COOH, preferably selected from sorbitan esters of 1,4- and/or 1,5-sorbitan and carboxylic acids R^(a)COOH, where R^(a) is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms, and where the weight ratio of the one or more compounds of the formula (I) to the one or more sorbitan esters just mentioned is from 70:30 to 100:0, preferably from 80:20 to 100:0, particularly preferably from 90:10 to 100:0 and especially preferably from 95:5 to 100:0. The stated weight ratio of “100:0” means that in this particularly preferred embodiment of the invention, the compositions A just mentioned do not need to comprise any sorbitan ester.

From among the compositions A just mentioned, preference is given to those in which the one or more sorbitan esters of sorbitan and carboxylic acids R^(a)COOH are selected from sorbitan esters of sorbitan and caprylic acid and are preferably selected from sorbitan esters of 1,4- and/or 1,5-sorbitan and caprylic acid and the sorbitan ester is particularly preferably sorbitan monocaprylate.

In these compositions A, the hydroxyl value of the mixture of the one or more compounds of the formula (I) and the one or more (if present) sorbitan esters of sorbitan and carboxylic acids R^(a)COOH is preferably smaller than or equal to 320, particularly preferably smaller than or equal to 285, especially preferably smaller than or equal to 245 and most preferably smaller than or equal to 225.

In a further particularly preferred embodiment of the invention, the hydroxyl value of the mixture of the one or more compounds of the formula (I) and the one or more compounds selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids in the compositions A is smaller than or equal to 320, preferably smaller than or equal to 285, particularly preferably smaller than or equal to 245 and especially preferably smaller than or equal to 225.

In a further particularly preferred embodiment of the invention, the compositions A do not comprise any compounds selected from sorbitol and sorbitol esters.

In a further particularly preferred embodiment of the invention, the compositions A do not comprise any compounds selected from sorbitan and sorbitan esters.

If the compositions A do comprise one or more compounds selected from the group consisting of sorbitol and sorbitol esters (where the carboxylic acid on which the acid component of these esters is based is preferably caprylic acid), these compounds together are preferably present in the compositions A in an amount smaller than or equal to 5.0% by weight, particularly preferably in an amount smaller than or equal to 3.0% by weight, especially preferably in an amount smaller than or equal to 1.0% by weight and most preferably in an amount smaller than or equal to 0.5% by weight, the stated % by weight in each case being based on the total weight of the finished compositions A.

If the compositions A do comprise one or more compounds selected from the group consisting of sorbitan and sorbitan esters (where the carboxylic acid on which the acid component of these esters is based is preferably caprylic acid), these compounds together are preferably present in the compositions A in an amount smaller than or equal to 20.0% by weight, particularly preferably in an amount smaller than or equal to 10.0% by weight, especially preferably in an amount smaller than or equal to 5.0% by weight and most preferably in an amount smaller than or equal to 1.0% by weight, the stated % by weight in each case being based on the total weight of the finished compositions A.

In a further particularly preferred embodiment of the invention, the compositions A comprise the one or more compounds of the formula (I) in amounts of at least 30% by weight, preferably in amounts of at least 50% by weight and particularly preferably in amounts of at least 60% by weight, in each case based on the total weight of the finished compositions A.

The hydroxyl value of a substance is to be understood as meaning that amount of KOH in mg equivalent to the amount of acetic acid bound during the acetylation of 1 g of substance.

Suitable determination methods for determining the hydroxyl value are, for example, DGF C-V 17 a (53), Ph. Eur. 2.5.3 Method A and DIN 53240.

In the context of the present invention, the hydroxyl values are determined analogously to DIN 53240-2. Here, the following procedure is adopted: 1 g, accurate to 0.1 mg, of the homogenized sample to be measured is weighed out. 20.00 ml of acetylation mixture (acetylation mixture: 50 ml of acetic anhydride are stirred into 1 liter of pyridine) are added. The sample is dissolved completely in the acetylation mixture, if required with stirring and heating. 5 ml of catalyst solution (catalyst solution: 2 g of 4-dimethylaminopyridine are dissolved in 100 ml of pyridine) are added. The reaction vessel is closed and placed into the water bath, preheated to 55° C., for 10 minutes, with mixing. 10 ml of fully deionized water are then added to the reaction solution, the reaction vessel is closed again and the mixture is once more allowed to react in the water bath with shaking for 10 minutes. The sample is cooled to room temperature (25° C.). 50 ml of 2-propanol and 2 drops of phenolphthalein are then added. This solution is titrated with aqueous sodium hydroxide solution (aqueous sodium hydroxide solution c=0.5 mol/l) (Va). Under identical conditions, but without any sample added, the efficacy of the acetylation mixture is determined (Vb).

From the aqueous sodium hydroxide solution consumed in the determination of the efficacy and the titration of the sample, the hydroxyl value (OHV) is calculated using the following formula:

${OHV} = \frac{\left( {{Vb} - {Va}} \right) \cdot c \cdot t \cdot M}{E}$

OHV=hydroxyl value in mg KOH/g substance Va=aqueous sodium hydroxide solution consumed in ml during the titration of the sample Vb=aqueous sodium hydroxide solution consumed in ml during the titration of the efficacy c=molar concentration of the aqueous sodium hydroxide solution in mol/l t=titer of the aqueous sodium hydroxide solution M=molar mass of KOH=56.11 g/mol E=sample weighed out in g

(Vb−Va) is that amount of aqueous sodium hydroxide solution used in ml, which is equivalent to the amount of acetic acid bound during the above-described acetylation of the sample to be measured.

Hereinbelow, the method just described for determining the hydroxyl value is referred to as “method OHV-A”.

Preferably, the use according to the invention is in cosmetic, dermatological or pharmaceutical compositions, in crop protection formulations, in washing or cleaning compositions or in paints or coatings. The crop protection compositions comprise one or more pesticides.

The cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings comprise the one or more compounds of the formula (I) preferably in amounts of from 0.01 to 10.0% by weight, particularly preferably in amounts of from 0.1 to 5.0% by weight and especially preferably in amounts of from 0.2 to 3.0% by weight, in each case based on the total weight of the finished cosmetic, dermatological or pharmaceutical compositions, crop protection formulations, washing or cleaning compositions or paints or coatings.

The cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings have viscosities preferably in the range from 50 to 200 000 mPa·s, particularly preferably in the range from 500 to 100 000 mPa·s, especially preferably in the range from 2 000 to 50 000 mPa·s and most preferably in the range from 5 000 to 30 000 mPa·s (20° C., Brookfield RVT, RV spindle set; 20 revolutions per minute).

The cosmetic, dermatological or pharmaceutical compositions are preferably present in the form of fluids, gels, foams, sprays, lotions or creams.

The cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings are preferably formulated on an aqueous or aqueous-alcoholic basis or are present as emulsions or dispersions. Particularly preferably, they are present as emulsions, and especially preferably they are present as oil-in-water emulsions.

As further auxiliaries and additives, the cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings may comprise all substances customarily used for the application in question, for example oils, waxes, emulsifiers, coemulsifiers, dispersants, surfactants, defoamers, solubilizers, electrolytes, hydroxy acids, stabilizers, polymers, film formers, further thickeners (different from the compounds of the formula (I)), gelling agents, superfattening agents, refattening agents, antimicrobially active compounds, biogenic active compounds, astringents, active substances, deodorizing substances, sun protection filters, antioxidants, oxidants, humectants, solvents, colorants, pigments, pearlizing agents, fragrances, opacifiers and/or silicones.

The cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings have a pH of preferably from 2 to 11, particularly preferably from 4.5 to 8.5 and especially preferably from 5.5 to 6.5.

The examples and applications which follow are intended to illustrate the invention in more detail, without, however, limiting it. All percentages are % by weight, unless explicitly stated otherwise.

Thickener performance was measured under the following conditions: Brookfield RVT; 20° C.; RV spindle set; 20 revolutions per minute

EXPERIMENTAL EXAMPLES A) Preparation of Isosorbide Caprylate

In a stirred apparatus with distillation head, 190.0 g (1.3 mol) of isosorbide (“Sorbon” from Ecogreen Oleochemicals) and 187.5 g (1.3 mol) of octanoic acid (caprylic acid) are initially charged at 80° C. together with 0.38 g of aqueous sodium hydroxide solution (18% by weight strength, aqueous) as catalyst. With stirring and under a flow of nitrogen (10-12 liters per hour), the reaction mixture is initially heated to 180° C., where the water of reaction begins to distill off. The reaction mixture is then heated to 190° C. over a period of 1 hour and to 210° C. over a further 2 hours. After 210° C. is reached, the esterification is continued until an acid value of <1 mg KOH/g is reached. This gives 345.7 g of amber isosorbide caprylate (97% of theory). The pH (5% by weight in ethanol/water 1:1) is 5.9. The pH was measured according to DIN EN 1262.

Further analytical characteristics of the isosorbide caprylate:

-   Acid value: 0.9 mg KOH/g, measured according to DIN EN ISO 2114 -   Hydroxyl value: 206 mg KOH/g, measured analogously to DIN 53240-2     according to method OHV-A -   Saponification value: 204 mg KOH/g, measured according to DIN EN ISO     3681

The isosorbide caprylate has the following composition:

Substance % by weight caprylic acid 0.4 isosorbide 18.1 isosorbide monocaprylate 50.9 isosorbide dicaprylate 30.6

Hereinbelow, this composition is referred to as “isosorbide caprylate 1”

B) Determination of the Thickener Performance of Isosorbide Caprylate 1

Using Genapol® LRO (sodium laureth-2 sulfate, 27% by weight in water) and Genagen® CAB 818 (cocamidopropyl betaine, 30% by weight in water) and additionally water, a 15% by weight mixture in water comprising the two surfactants in a weight ratio of 8:2 (hereinbelow referred to as “mixture 1”) is obtained. Various substances were added to this mixture 1, and the viscosity of the resulting compositions was determined. The results are shown in table 1 below.

TABLE 1 measured viscosities Added substance; amount Viscosity [% by weight] [mPa · s] NaCl [0.5% by weight] 40 NaCl [0.5% by weight] and isosorbide caprylate 1 [1% 330 by weight]

Various amounts of isosorbide caprylate 1 were added to mixture 1, and the viscosity of the resulting compositions was determined. The results are shown in table 2 below.

TABLE 2 measured viscosities Amount of isosorbide caprylate 1 added Viscosity [% by weight] [mPa · s] 0 5 0.2 6 0.4 10 0.6 12 0.8 21 1.0 12 1.2 37 1.4 34 1.6 45 1.8 55 2.0 72

It is evident from the results listed in tables 1 and 2 that isosorbide caprylate 1 has a thickening effect in aqueous surfactant systems.

C) Determination of the Thickener Performance of Isosorbide Caprylate 1

Using Genapol® LRO (sodium laureth-2 sulfate, 27% by weight in water) and Genagen® KB (cocobetain, 30% by weight in water) and additionally water, a 15% by weight mixture in water comprising the two surfactants in a weight ratio of 8:2 (hereinbelow referred to as “mixture 2”) is obtained. Various substances were added to this mixture 2, and the viscosity of the resulting compositions was determined. The results are shown in table 3 below.

TABLE 3 measured viscosities Added substance; amount Viscosity [% by weight] [mPa · s] NaCl [0.5% by weight] 3830 NaCl [0.5% by weight] and isosorbide caprylate 1 [1% 14200 by weight]

Various amounts of isosorbide caprylate 1 were added to mixture 2, and the viscosity of the resulting compositions was determined. The results are shown in table 4 below.

TABLE 4 measured viscosities Amount of isosorbide caprylate 1 added Viscosity [% by weight] [mPa · s] 0 135 0.2 310 0.4 460 0.6 875 0.8 1550 1.0 2510 1.2 4190 1.4 5650 1.6 6600 1.8 7400 2.0 7050

It is evident from the results listed in tables 3 and 4 that isosorbide caprylate 1 has a thickening effect in aqueous surfactant systems.

D) Determination of the Thickener Performance of Isosorbide Caprylate 1

An emulsion as indicated in table 5 below was prepared, and various concentrations of isosorbide caprylate 1 were added. The viscosities of the resulting emulsions were determined. The results are shown in table 5 below.

TABLE 5 measured viscosities Composition 1 2 3 4 Hostaphat ® KL 340 D (A) 1 1 1 1 trilaureth-4 phosphate mineral oil n.v. (A) 8 8 8 8 isopropyl palmitate (A) 3 3 3 3 Lanette ® O (A) 0.5 0.5 0.5 0.5 cetearyl alcohol Myritol ® 318 (A) 2 2 2 2 caprylic/capric triglyceride Tegin ® M (A) 0.5 0.5 0.5 0.5 glyceryl stearate isosorbide caprylate 1 (A) — 0.5 1.0 1.5 Aristoflex ® AVC (B) 0.4 0.4 0.4 0.4 ammonium acryloyldimethyltaurate/VP copolymer water (C) 71.6 72.1 71.6 71.1 glycerol (C) 5 5 5 5 alcohol (D) 5 5 5 5 tocopheryl acetate (D) 1 1 1 1 SilCare ® Silicone 41M15 (D) 1 1 1 1 caprylyl methicone Nipaguard ® PDU (E) 1 1 1 1 diazolidinylurea, methylparaben, propylparaben, propylene glycol pH measured 6.34 6.21 6.12 6.20 viscosity [mPa · s] 1860 2260 3130 3200

Preparation:

-   I The components of A are mixed and the mixture is heated to 60° C. -   II The components of C are mixed and the mixture is heated to 60° C. -   III B is added to I -   IV II is added to III and the mixture is stirred until it has cooled     to room temperature -   V The components D are gradually added to IV -   VI E is added to V, and the emulsion is homogenized

It is evident from the results listed in table 5 that isosorbide caprylate 1 has a thickening effect in emulsions.

E) Comparative Experiment

The thickener performance of isosorbide caprylate 1 in mixture 2 was compared, firstly, to a composition comprising 89.6% by weight of isosorbide dicaprylate and 9.4% by weight of isosorbide monocaprylate (remainder: 1% by weight) (hereinbelow referred to as “isosorbide dicaprylate”) and, secondly, to pure isosorbide. The results are shown in table 6.

TABLE 6 measured viscosities Substance added to mixture 2; amount Viscosity [% by weight] [mPa · s] none 135 isosorbide caprylate 1 [1% by weight] 2510 isosorbide dicaprylate [1% by weight] 2390 isosorbide [1% by weight] 160

As is evident from the results of table 6, the thickener performance of isosorbide is not worth mentioning, whereas isosorbide dicaprylate causes significant thickening.

However, as is also evident from the results of table 6, isosorbide caprylate 1 causes thickening comparable to that of isosorbide dicaprylate. If the thickener performance of isosorbide caprylate 1 were due only to the isosorbide dicaprylate comprised therein, the viscosity when using isosorbide caprylate 1 would have to be markedly lower that when isosorbide dicaprylate is used, since isosorbide caprylate 1 comprises only 30.6% by weight of isosorbide dicaprylate. Since the thickener performance of the isosorbide present in isosorbide caprylate 1 (as already mentioned above) is not worth mentioning and the possible thickening by the caprylic acid present in isosorbide caprylate 1 is negligible because of its small amount, but the thickener performance of isosorbide caprylate 1 is nevertheless comparable to the thickener performance of isosorbide dicaprylate, the compound isosorbide monocaprylate present in isosorbide caprylate 1 must have a significant thickener performance.

F) Use Examples

The use according to the invention can take place, for example, in the following formulations.

Formulation Example 1 Very Gentle EO- and Sulfate-Free Shampoo

% by Phase Ingredient weight A water ad 100 B sorbitol 1.0 C Hostapon ® SG 30.0 sodium cocoyl glycinate 15.0 Genagen ® KB coco-betaine Plantacare ® 818 UP 9.23 coco glucoside isosorbide caprylate 1 1.0 D lactic acid 25% by weight strength in water 3.25 E preservative q.s.

Preparation:

-   I B is added to A and the mixture is stirred until a clear solution     is obtained -   II C is added to I and the mixture is stirred until the solution is     homogeneous -   III The pH is adjusted to 7.0-7.2 using D -   IV E is added to III

Formulation Example 2 Gentle Facial Cleanser

% by Phase Ingredient weight A water ad 100 glycerol 20.0 B Hostapon ® SG 34.0 sodium cocoyl glycinate lauric acid 1.0 myristic acid 0.25 stearic acid 0.25 isosorbide caprylate 1 1.0 C lactic acid 0.90 water 6.80 D Genagen ® CAB 10.0 cocamidopropyl betaine E preservative q.s. fragrance q.s.

Preparation:

-   I Phase A is mixed and heated to 80° C. -   II The components of B are added gradually to I and stirring is     continued at 80° C. -   III Phase C is mixed and added to II -   IV The mixture is allowed to cool to 60° C., and D is added to III -   V At 40° C., E is added to IV

Formulation Example 3 Dishwashing Liquids

Ingredient % by weight Hostapur ® SAS 60 40.0 (alkanesulfonate, 60% by weight in water) Hostapur ® OS liquid 11.0 (sodium C14-16 alkyl sulfonate, 40% by weight in water) isosorbide caprylate 1 1.0 Genagen ® CAB 3.0 (cocoamidopropyl betaine, 30% by weight in water) preservative q.s. water ad 100

Formulation Example 4 Surface Cleaners (all-Purpose Cleaners)

Ingredient % by weight Hostapur ® SAS 60 5.0 (alkanesulfonate, 60% by weight in water) Genapol ® UD 080 2.0 (undecanol + 8 EO) isosorbide caprylate 1 1.0 preservative q.s. water ad 100

Preparation of formulation examples 3 and 4:

Half of the amount of water is initially charged and the components are stirred in in the same order as listed in the tables. The remaining amount of water is then added. This gives clear aqueous compositions. 

1-14. (canceled)
 15. A method of thickening cosmetic, dermatological or pharmaceutical compositions, crop protection formulations, washing or cleaning compositions or paints or coatings, said method comprising adding to said compositions, formulations, paints, or coatings of one or more compounds of the formula (I)

in which R is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight 10 chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms as thickeners.
 16. The method of claim 15, wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 to 9 carbon atoms.
 17. The method of claim 16, wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 carbon atoms.
 18. The method of claim 15, wherein the one or more compounds of the formula (I) are used in a composition comprising one or more other substances are selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids.
 19. The method of claim 18, wherein the composition comprises one or more compounds of the formula (I) and additionally I) isosorbide and II) one or more isosorbide diesters of the formula (II)

where R has the meaning given for formula (I) and where the isosorbide diester is preferably isosorbide dicaprylate.
 20. The method of claim 18, wherein the composition comprises one or more compounds of the formula (I) and additionally I) from 0.05 to 0.7, preferably from 0.1 to 0.7 and particularly preferably from 0.2 to 0.5 part by weight of isosorbide and II) from 0.1 to 1.0, preferably from 0.2 to 1.0 and particularly preferably from 0.4 to 0.8 part by weight of the one or more isosorbide diesters of the formula (II), where the isosorbide diester is preferably isosorbide dicaprylate, in each case based on 1.0 part by weight of the one or more compounds of the formula (I) and preferably based on 1.0 part by weight of isosorbide monocaprylate.
 21. The method of claim 18, wherein the composition comprises one or more compounds of the formula (I) and one or more sorbitan esters of sorbitan and carboxylic acids R^(a)COOH, preferably selected from sorbitan esters of 1,4- and/or 1,5-sorbitan and carboxylic acids R^(a)COOH, where R^(a) is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms, and the weight ratio of the one or more compounds of the formula (I) to the one or more sorbitan esters just mentioned is from 70:30 to 100:0, preferably from 80:20 to 100:0, particularly preferably from 90:10 to 100:0 and especially preferably from 95:5 to 100:0.
 22. The method of claim 21, wherein the one or more sorbitan esters of sorbitan and carboxylic acids R^(a)COOH are selected from sorbitan esters of sorbitan and caprylic acid and are preferably selected from sorbitan esters of 1,4- and/or 1,5-sorbitan and caprylic acid and the sorbitan ester is particularly preferably sorbitan monocaprylate.
 23. The method of claim 18, wherein the hydroxyl value of the mixture of the one or more compounds of the formula (I) and the one or more compounds selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids is smaller than or equal to 320, preferably smaller than or equal to 285, particularly preferably smaller than or equal to 245 and especially preferably smaller than or equal to
 225. 24. The method of claim 18, wherein the composition comprises the one or more compounds of the formula (I) in amounts of at least 30% by weight, preferably in amounts of at least 50% by weight and particularly preferably in amounts of at least 60% by weight, in each case based on the total weight of the finished composition.
 25. The method of claim 15, wherein the cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings comprise the one or more compounds of the formula (I) in amounts of from 0.01 to 10.0% by weight, preferably in amounts of from 0.1 to 5.0% by weight and particularly preferably in amounts of from 0.2 to 3.0% by weight, in each case based on the total weight of the finished cosmetic, dermatological or pharmaceutical compositions, crop protection formulations, washing or cleaning compositions or paints or coatings.
 26. The method of claim 15, wherein the cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings are formulated on an aqueous or aqueous-alcoholic basis or are present as emulsion or dispersion and preferably as emulsion.
 27. The method of claim 15, wherein the cosmetic, dermatological or pharmaceutical compositions, the crop protection formulations, the washing or cleaning compositions or the paints or coatings have a pH of from 2 to 11, preferably from 4.5 to 8.5 and particularly preferably from 5.5 to 6.5. 